I know a measly dollar isn't what gets you out of bed in the morning, but hear me out.

Early on when starting a business project, it's all too easy to get trapped in overanalysis—a mindless cycle of perfectionism and overwhelm devoid of any clear course of action. How do I know this? Because I was that guy.

Overcoming this loop requires a manual override.

The faster you get to the point of monetization, the easier it is to ward off the negative feelings that make you question the idea altogether.

Getting your first sale (or client) is the adrenaline injection that saves your project from a slow, bloody death on the boulevard of broken dreams.

It's a signpost pointing to the peak, affirming you're on the right trail.

Once you figure out the skills you need to make a dollar, it’s easy to replicate that process to make $1000, $10000 and beyond. 

My journey to making my first dollar starts out when I was a university student living in Ottawa, Canada.

A Complete Reset for a Worn Out University Graduate

What I thought I wanted to do was go to medical school, but what I actually wanted to do was something different. I just didn’t know it yet.

It was exam time in my senior year of university, and I was ready for a change. I’d been locked up in libraries, dreaming about exams and standardized test scores for what seemed like an eternity. By the end, it was as if I hadn’t seen the light of day for months. What I needed was a sabbatical.

While classmates were stressing over applications or starting up new careers, I started telling everyone I was going to Asia. The plan was to go for a year and apply to med schools while I traveled a bit and took a job teaching English.

Project: Relocation

Sure enough, a month a half later I was on the ground in Busan, South Korea—a coastal city of 4.5 million, the second largest after the capital of Seoul.

Moving to Asia was a completely alienating yet strangely reinvigorating experience that marked the beginning of an unforgettable chapter of my life. Until then, I’d only really ever existed in this one tiny radius on the map between my hometown and university city (aside from a few short trips to the northern States and British Columbia).

Here I was, dropped in a foreign land faced with new realities: staring strangers, jam-packed sidewalks, glowing neon signs, strange letters. No ability to communicate.

I was immediately forced to think differently.

Looking back, the whole thing was like a hard reset to my operating system. I went in one person, and came out another.

Once I broke through the initial hypnosis, I was hit with a huge new wave of motivation. All the things I couldn't make time for as a student suddenly felt easy to do.

I read non-fiction books, joined Toastmasters (a public speaking group), studied online marketing programs, learned the local language and worked on med school applications. Things were getting done!

New Mastermind Group in Asia

As time went on ended up meeting a few others who had newly relocated to Asia and were on a similar get sh\t done* buzz. A group of us became good friends and started hanging out regularly, meeting for meals in the evenings and going out for beers on the weekends.

Thanks in part to these connections, I stumbled upon cool new opportunities that forced me to get out of my comfort zone. I taught at a university and at several big companies, and was even offered gigs to act in television commercials for Korean multinationals like Samsung and Kia.

The weekly meetups with my new friends soon became formalized. We had all read Think and Grow Rich, a book which influenced us start up our own small mastermind group. We shared our goals with the group every week and tracked them through Google spreadsheets. The rules were simple: if you don't hit your goals, you had to pay up. The idea was to make not taking action more painful than just doing it.

Though my mindset on goal setting has shifted over time, there's no doubt these early "Money Challenges" pushed me to take massive action

What started out as general goals quickly shifted to goals about financial success and entrepreneurship. This is where things got interesting.

My Early Internet Marketing Experiences and Tools

Up until then, I had dabbled in website creation but I still hadn’t followed through on a project that had made me any money. Instead, I found myself starting something new, losing motivation and then moving on within a few weeks.

A classic case of entrepreneurial ADHD. 

I had built a Blogger blog in the weeks before I moved to Korea, partly because I wanted to document my experiences, and partly because I'd heard there was potential to make money from blogging.

In the end, the only people that read it were my friends from back home.

It wasn't until I came across Eben Pagan—an analytical marketing guru who ran his own seminars—that my luck started to change. After studying a few of his programs, I was completely sold on the idea that I could create my own income by building websites (a reality further solidified by reading The Four Hour Workweek and meeting others who were living nomadic lifestyles thanks to their internet businesses).

Before I'd ever delved into internet marketing, I had assumed that building a website required coding skills. I'm super grateful that one of my friends was able to help me build my first Wordpress website, but after ideas kept popping up I quickly realized I needed to know how to do that myself. So I found some tools to help me do that.

Here's what I used to build my own websites (and businesses) when I was starting out:

• Wordpress | Free open source website & blog building software that powers 70% of the websites on the internet
• Mailchimp | A free-to-use email service that allowed me to collect email addresses and communicate with my list en masse
• Bluehost | Cheap, reliable hosting service that kept the websites up and alive on the internet
• OptimizePress | A what-you-see-is-what-you-get landing page and website builder that made it possible to design my sites and collect email addresses easily
• Paypal | The service I used to collect payments

By the time we started out mastermind group, I had several websites up online but no one was visiting them. My problem was a traffic shortage.

The game changer for me was learning to get good at SEO—or search engine optimization—which involves preparing your content so it's more easily found by search engines.

Once I had that skill, I just needed the right project to apply it to.

The Site That Earned Me My First $8.10

One week during our mastermind meetup, we got to talking about renting apartments in Korea. While a lot of the expats in Korea had their housing arranged by their companies, my friend and I had both gone through the process of finding our own apartments there. Our friends had plenty of questions for us.

The Korean rental system is complicated.

There are two systems called joense and wolse—both of which involve putting down a large amount of cash as a deposit (usually at least $10,000 and sometimes upwards of $100,000) and going through a pile of paperwork to secure your money. This made things difficult for expats who didn't have massive sums of money in Korea, couldn't speak Korean, and didn't understand the system. If they wanted to secure their own housing, they were forced to pay grossly inflated rental fees to English speaking realtors who targeted them.

The idea was to start a website that educated people about the Korean real estate process.

We drove traffic by writing SEO optimized articles about topics that would help people looking for apartments in Korea, such as:

• Which areas to live in
• The cost of renting Korean apartments 
• Korean phrases to use when renting apartments
• How the key money systems work in Korea

On the site, we put up a free PDF guide that broke down three critical things expats needed to know to rent an apartment in Korea. The website visitors entered their emails to get the guide, and then were put on an autoresponder series.

The first email asked them what problems they were experiencing, and we offered to help them directly. The emails dripped out every week and were filled with tips and examples of how to go through the process. Every once in a while, we'd casually link to our product.

To this date, I still remember getting this notification. I sprung out of bed, glanced at my phone, and there it was: You received a payment of $17.00.

The notification of our first sale for our apartment rental guide

After Paypal took their cut and after my friend and I split the profits, my take home was eight dollars and ten cents. I was seriously ecstatic.

Lessons I Learned From Making My First Dollar

I can't emphasize enough how motivating it was to make my first dollar, and anyone else can tell you the same. To me, it was a tangible confirmation that I'd created value for someone else—so much so that they were willing to take out their credit card and exchange their hard-earned money for it (while I was sleeping even).

Here's what I learned in the process:

• Focus on giving value

In my early project, I created content around topics that I wanted to talk about. When my friend and I shifted our primary focus to creating solutions for others, we achieved success faster. I do think there's a sweet spot to be achieved that bridges the gap between your interests and the needs of others. It's more of bigger picture mindset shift to a frame of collaboration with others and meeting them where they're at. Getting good at SEO is essentially the same process: find what people are already searching for and create high quality content that helps them, allowing your passion for the topic to shine through.

• Ask your potential customers what they need

By focusing on walking our early email subscribers through the rental process, we were able to hone in on the exact issues they were experiencing. We literally asked them. It was through this process that we came up with the entire outline for our product. The readers were grateful for our help, and some even returned to purchase our product as a way of saying thanks. 

• Ratchet up skills step by step

I spent too much time in the beginning stages focused on learning and not enough time doing. I made much faster progress when I cut my focus to only learn what I needed to get to the next step. One piece of the puzzle at a time. Skills I’m glad I learned early: website building, SEO and email marketing.

• Your social circle is everything

For me, the change of environment meant that I had a brand new set of direct influences around me. The accountability and support I got from my friends during that period was invaluable. You’re going to become more like the people you hang around regularly. Choose that group wisely.

• Build on Wordpress

If you’re considering using any other platform for your website or blog, know that a lot of people eventually switch to Wordpress for its functionality. Consider using it from day one to save yourself the trouble. If you are confused about the setup, let me know and I’m happy to point you in the right direction. (Note: For ecommerce businesses, look into Shopify.)

• Monetize early

Internet marketing is a process of trial and error—the faster you test your ideas, the faster you can get feedback and adjust course. Monetizing early helps make your project more likely to succeed. Put your solutions out there quickly, charge for them and get feedback.

What Happened After I Made My First Dollar 

Making my first sale gave me the confidence that what I was learning really worked and the entire thing wasn’t merely a pipe dream. I became eager to double down on my ideas. 

I was still applying to medical schools, but a new goal was slowly forming in the back of my mind: I wanted a business, and I wanted to be able to run it from anywhere. 

We continued working on this apartment rental website for more than a year, expanding our efforts to consulting and forming partnerships with local realtors.

Looking back, the apartment site was the perfect starter project. It allowed me to learn the skills I needed to make money online and prove to myself that it was possible. It also gave me the confidence to extend my Asian travels for another year to chase my dream of having my own company.

A few months later, a spark of inspiration hit me for a brand new project with a bigger, grander vision that ended up shifting my focus. That's where the next story picks up.

I’m curious, how did you make your first dollar online?